In 1912, Little Jack opened an insurance brokerage in Number 11, Passchendale. In 1942, Little Jack died and the business was taken over by his son D.R. (Donald Rory) MacKenzie, who was well known in the horse racing circuit and was also the town jailer and a town councilor while running the business. He moved the office to what is now a heritage building, the old town hall. He passed away in 1972 and his son Jack took over the business, which was now on Catherine Street. Jack’s son Donnie took the reins in 1989 and he moved into the current location the next year. MacKenzie Insurance joined the MacLeod Lorway team in 1995.